Next Article in Journal / Special Issue
Investigation of Structural Dynamics of Enzymes and Protonation States of Substrates Using Computational Tools
Previous Article in Journal
Co-Assembled Supported Catalysts: Synthesis of Nano-Structured Supported Catalysts with Hierarchic Pores through Combined Flow and Radiation Induced Co-Assembled Nano-Reactors
Previous Article in Special Issue
Role of Conformational Motions in Enzyme Function: Selected Methodologies and Case Studies
Article Menu

Export Article

Open AccessArticle
Catalysts 2016, 6(6), 78; doi:10.3390/catal6060078

Solvent-Free Lipase-Catalyzed Synthesis of Technical-Grade Sugar Esters and Evaluation of Their Physicochemical and Bioactive Properties

1
Department of Biosystems Engineering and Soil Science, University of Tennessee, Knoxville, TN 37996-4531, USA
2
MARC-IV Consulting Inc., 101 East Main Street, Kearney, MO 64060, USA
3
Key Laboratory of Food Nutrition and Safety, Ministry of Education, College of Food Engineering and Biotechnology, Tianjin University of Science and Technology, Tianjin 300457, China
4
Department of Food Science, Pennsylvania State University, University Park, PA 16802, USA
*
Author to whom correspondence should be addressed.
Academic Editors: David D. Boehr and Keith Hohn
Received: 24 March 2016 / Revised: 6 May 2016 / Accepted: 17 May 2016 / Published: 30 May 2016
(This article belongs to the Special Issue Enzyme Catalysis)
View Full-Text   |   Download PDF [1585 KB, uploaded 30 May 2016]   |  

Abstract

Technical-grade oleic acid esters of sucrose and fructose were prepared using solvent-free biocatalysis at 65 °C, without any downstream purification applied, and their physicochemical and bioactivity-related properties were evaluated and compared to a commercially available sucrose laurate emulsifier. To increase the conversion of sucrose and fructose oleate, prepared previously using solvent-free lipase-catalyzed esterification catalyzed by Rhizomucor miehei lipase (81% and 83% ester, respectively), the enzymatic reaction conditions was continued using CaSO4 to control the reactor’s air headspace and a lipase (from Candida antarctica B) with a hydrophobic immobilization matrix to provide an ultralow water activity, and high-pressure homogenation, to form metastable suspensions of 2.0–3.3 micron sized saccharide particles in liquid-phase reaction media. These measures led to increased ester content of 89% and 96% for reactions involving sucrose and fructose, respectively. The monoester content among the esters decreased from 90% to <70% due to differences in regioselectivity between the lipases. The resultant technical-grade sucrose and fructose lowered the surface tension to <30 mN/m, and possessed excellent emulsification capability and stability over 36 h using hexadecane and dodecane as oils, comparable to that of sucrose laurate and Tween® 80). The technical-grade sugar esters, particularly fructose oleate, more effectively inhibited gram-positive foodborne pathogens (Lactobacillus plantarum, Pediococcus pentosaceus and Bacillus subtilis). Furthermore, all three sugar esters displayed antitumor activity, particularly the two sucrose esters. This study demonstrates the importance of controlling the biocatalysts’ water activity to achieve high conversion, the impact of a lipase’s regioselectivity in dictating product distribution, and the use of solvent-free biocatalysis to important biobased surfactants useful in foods, cosmetics, personal care products, and medicine. View Full-Text
Keywords: antimicrobial activity; antitumor activity; emulsification; high-pressure homogenation; lipase; sugar-fatty acid esters; surfactants antimicrobial activity; antitumor activity; emulsification; high-pressure homogenation; lipase; sugar-fatty acid esters; surfactants
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Ye, R.; Hayes, D.G.; Burton, R.; Liu, A.; Harte, F.M.; Wang, Y. Solvent-Free Lipase-Catalyzed Synthesis of Technical-Grade Sugar Esters and Evaluation of Their Physicochemical and Bioactive Properties. Catalysts 2016, 6, 78.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Catalysts EISSN 2073-4344 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top